An Initial Study of the Catalytic Reforming of Crop Oil‐Derived 1‐Alkenes with HZSM‐5 to Aromatic Hydrocarbons

Abstract

AbstractThis study explored the production of aromatic hydrocarbons from the longer‐chain alkenes produced by the pyrolysis/cracking of crop oils. 1‐Tetradecene, serving as a model compound for these alkenes, was reformed in a batch reactor with a HZSM‐5 catalyst to produce a liquid hydrocarbon mixture with a high‐aromatic content. These reactions resulted in a >99% conversion of the 1‐tetradecene feedstock with a yield of up to 22 wt% of aromatic hydrocarbons. Surprisingly, isomers of C3‐substituted benzenes along with xylenes and diaromatics (lower homologs of alkyl‐substituted indanes and naphthalenes) were the main aromatic products rather than their lower‐molecular‐weight (MW) homologs, benzene, toluene, ethylbenzene and xylenes, which are commonly formed with high selectivity during zeolite‐catalyzed reforming. The recovery of higher‐MW aromatics, and particularly bicyclic naphthalenes and indanes, provides mechanistic insights for zeolite‐catalyzed alkene reforming reactions suggesting that these higher‐MW aromatics are likely formed near the catalyst surface at pore openings. Furthermore, the production of acyclic diene intermediates in the size range of C7–C10 provides insight into the overall reaction pathway. The results suggest that this reaction pathway may be a commercially viable option for the production of renewable C3‐substituted aromatic chemicals/chemical intermediates as coproducts to complement the kerosene and diesel fuel blendstocks that are the primary products from crop oil cracking.